US4978382A - Pesticides based on 2-halogenoalkylthio-substituted pyrimidine derivatives - Google Patents

Pesticides based on 2-halogenoalkylthio-substituted pyrimidine derivatives Download PDF

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US4978382A
US4978382A US07/408,850 US40885089A US4978382A US 4978382 A US4978382 A US 4978382A US 40885089 A US40885089 A US 40885089A US 4978382 A US4978382 A US 4978382A
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pyrimidine
formula
halogenoalkyl
compound
methyl
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Udo Kraatz
Ernst Kysela
Jurgen Hartwig
Benedikt Becker
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/58—Two sulfur atoms

Definitions

  • the invention relates to the use of 2-halogenoalkylthio-substituted pyrimidine derivatives, some of which are known, as active compounds in pesticides, novel 2-halogenoalkylthio-substituted pyrimidine derivatives, and a process for the preparation thereof.
  • 2-halogenoalkylthio-substituted pyridines such as, for example, 2-(dibromofluoromethylthio)-pyridine, possess insecticidal properties (cf. DE-A No. 3,510,178).
  • 2-halogenoalkylthio-substituted pyrimidines such as, for example, 2-(chloromethylthio)-5-chloropyrimidine and 2-(iodomethylthio)-5-chloropyrimidine, are known as intermediates for the preparation of pharmaceutical products (cf. EP-A No. 0,033,195).
  • 2-substituted thio-4,5-diarylpyrimidines are known, such as, for example, 2-(1,1,2,2-tetrafluoromethylthio)-4,5-bis(4-methoxyphenyl)-pyrimidine and 2-trifluoromethylthio-4,5-bis(4-fluorophenyl)-pyrimidine.
  • These compounds have, inter alia, a powerful anti-inflammatory and analgesic action (cf. U.S. Pat. No. 4,438,117).
  • R represents hydrogen, alkyl, alkylthio, alkoxy, halogenoalkyl, halogenoalkylthio, halogenoalkgxy, optionally substituted aryl or halogen, and
  • n a number 0, 1, 2 or 3
  • insects are highly effective against animal pests, in particular against insects, arachnids and nematodes. They are therefore suitable as active compounds in pesticides, in particular as insecticides, acaricides and nematicides.
  • the 2-halogenoalkylthio-substituted pyrimidine derivatives of the general formula (I) which are to be used according to the invention show a better action as pesticides, in particular as insecticides, acaricides and nematicides, than 2-(dibromo-fluoromethylthio)-pyridine, which is known from the prior art.
  • the 2-halogenoalkylthio-substituted pyrimidine derivatives which are to be used according to the invention therefore represent a valuable enrichment of the art.
  • Formula (I) provides a general definition of the 2-halogenoalkylthio-substituted pyrimidine derivatives to be used according to the invention.
  • Compounds of the formula (I) which are preferably used as pesticides are those in which
  • R 1 represents halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms
  • halogenoalkyl represents hydrogen, in each case straight-chain or branched alkyl, alkylthio, alkoxy, halogenoalkyl, halogenoalkylthio or halogenoalkoxy, in each case having 1 to 4 carbon atoms and, in the case of halogenoalkyl, halogenoalkylthio and halogenoalkoxy, having 1 to 9 identical or different halogen atoms, furthermore represents phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents from the series comprising halogen, nitro, alkyl or alkoxy, in each case having 1 to 4 carbon atoms, or halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or also represents halogen, and
  • n a number 0, 1, 2 or 3.
  • R 1 represents halogenomethyl having 1 to 3 identical or different halogen atoms
  • R represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, methoxy, halogenoalkyl, halogenoalkylthio or halogenoalkoxy, in each case having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms; furthermore represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents from the series comprising fluorine, chlorine, bromine, nitro, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, or also represents halogen, and
  • n a number 0, 1, 2 or 3.
  • n a number 0, 1, 2 or 3 and
  • R 2 represents hydrogen, chlorine, bromine or iodine
  • Formula (Ia) provides a general definition of the 2-halogenoalkylthio-substituted pyrimidine derivatives according to the invention
  • Preferred compounds of the formula (Ia) are those in which
  • R represents hydrogen, in each case straight-chain or branched alkyl, alkylthio, alkoxy, halogenoalkyl, halogenoalkylthio or halogenoalkoxy, each having 1 to 4 carbon atoms and, in the case of halogenoalkoxyl, halogenoalkylthio and halogenoalkoxy, having 1 to 9 identical or different halogen atoms, furthermore represents phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents from the series comprising halogen, nitro, alkyl or alkoxy, each having 1 to 4 carbon atoms, or halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or also represents halogen,
  • R 2 represents hydrogen, chlorine or bromine
  • n represents a number 0, 1, 2 or 3, with the exception of the compounds 2-(difluoromethylthio)-4,6-dimethyl-pyrimidine, 2,4-bis(difluoromethylthio)-6-methylpyrimidine and 4-(difluoromethoxy)-2-(difluoromethylthio)-6-methylpyrimidine
  • Particularly preferred compounds of the formula (Ia) are those in which
  • R represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, methoxy, halogenoalkyl, halogenoalkylthio or halogenoalkoxy, each having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms; furthermore represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents from the series comprising fluorine, chlorine, bromine, nitro, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, or also represents halogen,
  • R 2 represents hydrogen, chlorine or bromine
  • m represents a number 0, 1, 2 or 3, with the exception of the compounds 2-(difluoromethylthio)-4,6-dimethyl-pyrimidine, 2,4-bis(difluoromethylthio)-6-methyl-pyrimidine and 4-(difluoromethoxy)-2-(difluoromethylthio)-6-methyl-pyrimidine.
  • R 2 has the abovementioned meaning
  • X represents halogen, preferably chlorine or bromine
  • the known compounds of the formula (I) may be prepared analogously to the process indicated above, for the preparation of the novel compounds of the formula (Ia).
  • Formula (II) provides a general definition of the 2-mercaptopyrimidines required as starting materials for carrying out the preparation process
  • R and the index m represent those meanings which have been indicated above in the description of the novel 2-(halogenomethylthio)-pyrimidine derivatives of the formula (Ia) for R and the index m.
  • the 2-mercaptopyrimidines of the formula (II) are known and/or can be prepared in a simple, analogous manner by known processes (cf. Coll. Czech. Chem. Commun., 24, 1667 (1959); Chem. Ber. 104, 2975 (1971) and U.S. Pat. No. 4,438,117).
  • Formula (III) provides a general definition of the alkyl halides furthermore required as starting materials for carrying out the preparation process.
  • R 2 and X have those meanings which have been indicated above in the description of the novel 2-(halogenomethylthio)-pyrimidine derivatives of the formula (Ia) for R 2 and X.
  • the compounds of the formula (III) are generally known compounds of organic chemistry.
  • novel compounds of the formula (Ia) are preferably prepared using diluents.
  • Suitable diluents in this process are water and virtually all inert organic solvents which are customary for the reaction. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers, such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones, such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, such as methyl acetate and e
  • alkali metal hydroxides such as, for example, sodium hydroxide and potassium hydroxide
  • alkaline earth metal hydroxides such as, for example, calcium hydroxide
  • alkali metal carbonates and alkali metal alcoholates such as sodium carbonate and potassium carbonate, sodium methylate, potassium methylate, sodium ethylate and potassium ethylate
  • hydrides such as, for example, sodium hydride, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo-[4,3,0]-non-5-ene (DBU), 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2,2,2]-octane (DABCO).
  • DBU 1,5-diazabicyclo-[4,3,0]-non-5-en
  • reaction temperatures can be varied in a relatively wide range. In general, the process is carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 70° C.
  • 1.0 to 10.0 moles, preferably 1.0 to 6.0 moles, of alkylating agent of the formula (III) and 1.0 to 8.0 moles, preferably 1.0 to 5.0 moles, of base are generally employed per mole of 2-mercaptopyrimidine of the formula (II).
  • the process for the preparation of the novel compounds of the formula (Ia) is generally carried out under atmospheric pressure. Under certain conditions, however, the process can also be carried out under increased or reduced pressure.
  • gaseous alkylating agents of the formula (III) are used, these compounds can be passed in through the mixture of diluent, compound of the formula (II) and base.
  • the reactions are carried out in a suitable diluent, and the reaction mixture is stirred for several hours at the particular temperature required
  • the reaction products of the formula (Ia) are worked up and isolated in a generally customary manner.
  • the active substances are suitable for combating animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field They are active against normally-sensitive and resistant species, and against all or individual development stages.
  • animal pests preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field They are active against normally-sensitive and resistant species, and against all or individual development stages.
  • the above-mentioned pests include:
  • Isopoda for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber.
  • Chilopoda for example, Geophilus carpophagus and Scutigera spec.
  • Symphyla for example, Scutigerella immaculata.
  • Thysanura for example, Lepisma saccharina.
  • Orthoptera for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.
  • Anoplura for example, Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.
  • Thysanoptera From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci.
  • From the order of the Homoptera for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
  • Bucculatrix thurberiella Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bissilliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana.
  • Hymenoptera From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.
  • Acarina for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp..
  • the plant-parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp. and Trichodorus spp..
  • the active compounds of the formula (I) to be used according to the invention are distinguished by an excellent insecticidal activity.
  • the excellent action against nematodes such as, for example, Globodera rostochiensis and Meloidogyne incognita
  • the active compounds according to the invention also show an excellent action against plant-damaging insects, such as, for example, Tetranychus species and Plutella caterpillars.
  • the active compounds can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans, fumigating coils and the like, as well as ULV cold mist and warm mist formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans, fumigating coils and the like, as well as ULV cold mist and warm mist formulations.
  • formulations are produced in known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
  • extenders that is, liquid solvents, liquefied gases under pressure, and/or solid carriers
  • surface-active agents that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents there are suitable in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water; by liquefied gaseous extenders or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers
  • Adhesives such as carboxym-ethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dye-stuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments for example iron oxide, titanium oxide and Prussian Blue
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dye-stuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds to be used according to the invention can be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, pheromones, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active compounds such as insecticides, pheromones, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric acid esters, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorganisms, inter alia.
  • the active compounds to be used according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents.
  • Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.
  • the active compound content of the use forms prepared from the commercially available formulations can vary within wide limits.
  • the active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
  • the active compounds When used against hygiene pests and pests of stored products, the active compounds are distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • Compound (A) is disclosed in DE-A No. 2,510,178.
  • Test nematode Meloidogyne incognita
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the preparation of active compound is intimately mixed with soil which is heavily infested with the test nematodes.
  • concentration of the active compound in the preparation is of practically no importance here, only the amount of active compound per unit volume of soil, which is given in ppm, being decisive.
  • the treated soil is filled into pots, lettuce is sown and the pots are kept at a greenhouse temperature of 27° C.
  • the lettuce roots are examined for infestation with nematodes (root galls), and the degree of effectiveness of the active compound is determined in %.
  • the degree of effectiveness is 100% if infestation is completely avoided and is 0% if the infestation is just as high as in the case of the control plants in untreated soil which has been infested in the same manner.
  • Test nematode Globodera rostochiensis
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the preparation of active compound is intimately mixed with soil which is heavily infested with the test nematodes.
  • concentration of the active compound in the preparation is of practically no importance here, only the amount of active compound per unit volume of soil, which is given in ppm, being decisive.
  • the treated soil is filled into pots, potatoes are planted and the pots are kept at a greenhouse temperature of 18° C.
  • the potato roots are examined for cysts, and the degree of effectiveness of the active compound is determined in %.
  • the degree of effectiveness is 100% if infestation is completely avoided and is 0% if the plants in untreated soil which has been infested in the same manner.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Bean plants Phaseolus vulgaris which are heavily infested with all developmental stages of the common spider mite or greenhouse red spider mite (Tetranychus urticae) are treated by dipping into the active compound preparation of the desired concentration.
  • the destruction is determined in 100% means that all the spider mites have been killed; 0% means that none of the spider mites have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are infested with caterpillars of the diamond-back moth (Plutella maculipennis), as long as the leaves are still moist.
  • the destruction in % is determined. 100% means that all the caterpillars have been killed; 0% means that none of the caterpillars have been killed.
  • Test insect Diabrotica balteata-larvae in the soil
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the preparation of active compound is intimately mixed with the soil.
  • the soil is filled into 0.5 l pots and the pots are left to stand at 20° C.
  • pregerminated corn seeds are planted in each of the pots. After 2 days the appropriate test insects are inserted into the treated soil. After further 7 days the degree of effectiveness of the active compound is determined in % by counting the dead and the live test insects. The degree of effectiveness is 100% if all of the test insects have been killed and 0% if exactly as many insects are still alive as in the case of the untreated control.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
US07/408,850 1988-09-24 1989-09-18 Pesticides based on 2-halogenoalkylthio-substituted pyrimidine derivatives Expired - Fee Related US4978382A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3832530 1988-09-24
DE3832530 1988-09-24
DE3912155 1989-04-13
DE3912155A DE3912155A1 (de) 1988-09-24 1989-04-13 Schaedlingsbekaempfungsmittel auf basis von 2-halogenalkylthio-substituierten pyrimidin-derivaten

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ES (1) ES2055769T3 (fr)

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Publication number Priority date Publication date Assignee Title
US6893815B1 (en) * 1997-06-30 2005-05-17 Isis Pharmaceuticals, Inc. Nucleobase heterocyclic combinatorialization
US20070248636A1 (en) * 2006-04-25 2007-10-25 Higbee Bradley Method for achieving increased effectiveness when using a synthetic pheromone composition to cause mating disruption among insect pests

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
KR100389377B1 (ko) * 2000-07-20 2003-06-25 한국전력공사 고전압 분압 및 전류 공급용 전왜 세라믹스 조성물 및 제조방법

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EP0033195A1 (fr) * 1980-01-10 1981-08-05 NYEGAARD & CO. A/S Pyrimidine-2-thioéthers et leurs S-oxydes pour l'application thérapeutique, compositions pharmaceutiques les contenant, procédés pour leur préparation ainsi que composés en soi au cas où ils sont nouveaux
US4438117A (en) * 1980-09-03 1984-03-20 E. I. Du Pont De Nemours And Company 2-Substituted thio-4,5-diarylpyrimidines
DE3510178A1 (de) * 1985-03-21 1986-09-25 Hoechst Ag, 6230 Frankfurt Neue halogenalkylthiosubstituierte heterocyclen, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz

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EP0033195A1 (fr) * 1980-01-10 1981-08-05 NYEGAARD & CO. A/S Pyrimidine-2-thioéthers et leurs S-oxydes pour l'application thérapeutique, compositions pharmaceutiques les contenant, procédés pour leur préparation ainsi que composés en soi au cas où ils sont nouveaux
US4438117A (en) * 1980-09-03 1984-03-20 E. I. Du Pont De Nemours And Company 2-Substituted thio-4,5-diarylpyrimidines
DE3510178A1 (de) * 1985-03-21 1986-09-25 Hoechst Ag, 6230 Frankfurt Neue halogenalkylthiosubstituierte heterocyclen, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6893815B1 (en) * 1997-06-30 2005-05-17 Isis Pharmaceuticals, Inc. Nucleobase heterocyclic combinatorialization
US20070248636A1 (en) * 2006-04-25 2007-10-25 Higbee Bradley Method for achieving increased effectiveness when using a synthetic pheromone composition to cause mating disruption among insect pests

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ES2055769T3 (es) 1994-09-01
DE3912155A1 (de) 1990-03-29
EP0361185A2 (fr) 1990-04-04
EP0361185B1 (fr) 1994-06-22
DE58907941D1 (de) 1994-07-28
KR900004255A (ko) 1990-04-12
JPH02129172A (ja) 1990-05-17
EP0361185A3 (en) 1990-10-24

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